22 The Essentials: Dolomites, Italy

The Dolomites are one of Italy’s most visually striking regions, but they require far more strategic planning than many travel advisors expect. In this episode, Italy specialist and Travel Advisor Karen Hattaway shares firsthand insight into how seasonality, elevation, and geography shape the client experience in the Dolomites. She explains when to send clients for summer hiking versus winter snow, which months to avoid entirely, and why July and August often work against the experience. The conversation also breaks down the key valleys, comparing well-known hubs like Cortina and Ortisei with more authentic alternatives such as Val di Fassa and Alta Badia. Travel Advisors will gain practical guidance on logistics, transportation, wellness culture, and client fit so they can confidently design Dolomites itineraries that feel intentional rather than overwhelming.

Key Takeaways

  • How to position summer versus winter travel in the Dolomites based on weather, crowds, and elevation

  • When to steer clients away from peak July and August in favor of late June or September sweet spots

  • Which valleys deliver luxury familiarity versus quieter, more authentic mountain culture

  • How to plan Dolomites itineraries around logistics, drive times, and realistic pacing

  • What to consider for non-skiers, families, and wellness-focused travelers in every season

About the guest: 

Karen Costa Hattaway is a Travel Advisor and the founder of Life Beyond the Room, a travel concierge company focused on designing immersive, culturally grounded journeys. She specializes in creating thoughtful itineraries that prioritize seasonality, local connection, and authentic experiences beyond the traditional luxury hotel stay. With deep expertise in Italy and alpine regions like the Dolomites, Karen brings a practical, on-the-ground perspective to helping travelers experience destinations in a way that feels intentional, meaningful, and deeply connected to place.

Links and Resources:

Whitney Shindelar

Undiscovered Sunsets was a long time in the making, even if I myself didn’t realize it. During my time at the University of Northern Iowa, I studied abroad in New Zealand. Upon graduating, I bought a one-way ticket to France, lived with a French family and studied with classmates from Turkey, China, Russia, Germany, Italy, and everywhere in between. In 2010 I began teaching English as a foreign language. This job quickly took me to China, where English teachers were in high demand and within three years, I began working in a 5-star hotel, speaking Mandarin throughout most of my day. In total, I lived abroad for 7 years.

I consider Undiscovered Sunsets to be the perfect mélange of my personal experience traveling the world and my professional experience working in the hospitality industry.

I look forward to designing your next adventure!

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23 The Essentials: Bordeaux, France 

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21 The Essentials: San Sebastian, Spain